


Turnabout's Fair Play

by mukur0



Category: Supernatural
Genre: Crowley's Big Dick, Deepthroating, FTM, M/M, PWP, Trans Sam Winchester, safe sex
Language: English
Status: Completed
Published: 2019-07-01
Updated: 2019-07-01
Packaged: 2020-05-31 18:17:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,341
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19431478
Author URL: https://archiveofourown.org/users/mukur0/pseuds/mukur0
Summary: PWP. Sam shoots Crowley and makes it up to him for his ruined suit. Crowley's a gentleman.





	Turnabout's Fair Play

**Author's Note:**

> Sam Winchester Bingo: oral square / Heaven & Hell Bingo: dead meatsuit square / Dark Bingo: fornication square / Bad Things Happen Bingo: forced to kneel square (it's not really forced but I had fun with it)
> 
> Beta'd by saunatonttu.
> 
> I struggled a lot with what vocabulary to use for Sam's bits and ended with what I use, as a trans guy. I hope it's comfortable for everybody.

“Oh, son of a whore, moose. You Winchesters are going to be the death of my wardrobe.” 

He even said it like he expected Sam to give a shit. He was, however, sorely disappointed, as the resident hunter only stepped around his newly insulated frame to toe the body on the floor. It twitched, gurgled, gave a death rattle that involved shaking so hard Sam almost shot it again, and fell still.

“What?” Sam muttered, grimacing. Crowley’d crossed his arms over the shower of silver birdshot in his chest and was giving him a flat glare, going so far as to tap his shoe’s silver toe on the cement floor to complete the picture. “He was right behind you. You didn’t move fast enough.”

“So my suit is acceptable collateral damage. Typical,” the demon tsked, already turned to give the body a resentful kick. “I’m going to start billing you. Shirt and blazer, Armani, tie, Neiman Marcus--”

Stowing his weapons stopped abruptly, Sam turning to cast an alarmed look over his shoulder. “Are you fucking kidding me? That has to be like two thousand dollars--”

“Try four, altogether, sweetums,” Crowley sneered in return. “That’s not counting the tailoring.”

He could feel his back going up already, hackles rising at this smarmy prick. But...that was what he wanted. Sam stuffed the rifle into his bag and turned back to the king of the crossroads, eyes narrowed. There was that twinkle in the demon’s eyes he knew all too well, and not for the first time he was glad Dean was on another hunt a state away. So this was why Crowley had insisted on bugging him all the way across the midwest.

_ “Well,” _ he chuckled, stepping in closer till he towered over that smirking son of a bitch, “I guess I’ll have to get creative and make it up to you.”

There it was, that self-satisfied, slimy grin that told him everything he needed to know. This asshole had been in the way on purpose and sacrificed a suit just for the excuse to flirt. Another time Sam would have teased him for being a little desperate, but at the moment he wasn’t exactly bothered.

“Oh?” drawled the demon, hands in his pockets. “Is that a sin I feel coming on, Sam Winchester?”

With the loudest laugh he’d probably had in a year, he knelt one knee at a time, already reaching for that shiny belt buckle, and carefully slid the leather strip out of its trappings. “I wouldn’t know,” he hummed with his nose buried in the twill around Crowley’s zipper, purring as he felt it begin to tighten. If Dean ever found out about all the times they’d done this he’d be a dead man.

When had all this even started? The last time he’d asked Crowley had waved a dismissive hand, and Sam...well, the flirting had gone on for a long time, in between periods of primal hatred, and then there was that time with the hate sex that was absolutely incredible, and he was going to be thinking about that in bed for a long time to come.

Crowley had always been attractive. The suave Scotsman thing, complete with fake British accent to really complete the sugar daddy vibe. Confident and a little bit lewd and a lot of innuendo. 

Then there was his dick. Now Sam didn’t consider himself a size queen, but  _ that _ was special.

“That’s a good moose,” Crowley purred, soft as velvet, running fingers through Sam’s hair with the easygoing smirk of a man with all the time in the world. Sam responded by nuzzling the growing head of his cock through his trousers, mouthing and nibbling with the fabric between them. “My good boy. I suppose I can forgive the suit if you really put your all into it, darling.”

He’d already learned that Sam’s stares were just as lethal from on his knees, but he only chuckled and motioned the man to get on with it. They had all night, but he didn’t have a lot of patience.

The trouser button came loose with a flick of a finger and he couldn’t resist using his teeth on the zipper, looking up through his eyelashes to appreciate the admiration in Crowley’s expression. The demon offered a shining circle of aluminum, smirking at the way Sam snatched it and tore it open with one hand, the other busy tugging down his trousers and boxers.

His mouth always watered at the sight of Crowley’s cock, and Crowley fucking knew it. He even laughed when Sam laid the “ultra-thin” condom against his lips and slid it on over his glans with his mouth. “Be a dear and do that thing I like with your tongue, Samuel.”

Grumbling, he did it nonetheless. Lips wrapped tight around the head of Crowley’s cock, tip of his tongue pressed to the sweep of the frenulum, he sucked hard and rubbed the flat of his tongue up the slit, quietly enjoying the way that the hand in his hair tightened and dug fingernails into his scalp.

The rest of the condom had to be rolled down with his fist, out of reach of his mouth for now. His lips popped off with a loud suck so he could lick the devil’s balls in long, slow strips, enjoying the tickle of neatly-trimmed pubic hair against his cheeks. With a soft moan Crowley pressed his hips forward, trying to push his cock against Sam’s mouth, but he withdrew with a wicked grin and gave another stroke with his hand while his tongue teased the seam between his testes. How the hell did he keep all this in his pants? Every time he saw it he wondered the same thing.

Growling out his frustration, the king of the crossroads gripped Sam’s hair hard, forcing his head still so he could rut his shaft against one of Sam’s cheeks, the latex dragging near painfully on his skin. With a laugh that was a little mean he pulled away, batting Crowley’s hands away, and obliged with his tongue lapping long stripes up the thick underside of his length.

He’d learned that Crowley liked the almost-pain--he wanted to be squeezed a bit too tight, for Sam’s teeth to drag over him, to hold his balls in one hand and grip them till Crowley sighed happily in one long gust of overheated breath. He kissed lines across his cock, teased his nose around the ridge of his glans while he licked shapes up the shaft, made an o with his thumb and finger and tightened it hard around the base of his cock so it twitched and hardened even further under his nibbles.

Eventually he’d overstayed his welcome. Grinning breathlessly, cheeks rosy, looks complete with a line of saliva running down his chin, Sam only returned his glare with a purr. “Get to it, pet,” Crowley hissed, but he was smiling himself, and at the end he didn’t bother to hide a fond chuckle. He stroked Sam’s hair like a particularly dear cat, watching so keenly at the way he finally  _ (finally) _ slid the head into his mouth and leaned in deeper.

It always took time, and he almost always managed it, breath even, hands steadying himself against Crowley’s bare hips. His eyes stung with unshed tears, but finally he swallowed and had his throat open, head pushing forward till he could feel the girth stretching open his throat. It fluttered around the invasion; the tears fell, tracking down his cheekbones, and he dug his fingers into the ready flesh under his fingernails. 

The demon hadn’t broken eye contact the entire time. He smiled, encouraging, cooing sweet nonsense, but Sam had to close his eyes and draw back, shivering as he sucked in a huge breath and dove in again, faster this time, taking him as far as before and then further, only satisfied when he felt curly hair against his nose and the rim of the condom against his lips.

“Oh,  _ Sam,” _ Crowley purred. “Darling, you’re a wonder as always. Come on, look at me, let me see those pretty eyes.”

A second to be sure he wasn’t gagging and he forced his eyes open. More tears spilled, just like he knew Crowley adored, as he began to move back and forth, finding a speed and position that allowed him quick snatches of breath at the furthest. Honestly, he didn’t particularly enjoy deepthroating, and especially not such a big cock, but  _ God _ did he love pleasing a partner, and that overrode any of the discomfort and more. The latex was high-end and only had a touch of the latex bite, but even so he’d have to brush his teeth after to get rid of it--and even so it was absolutely fucking worth every moment.

And it was working. The king of the fucking crossroads was moaning, his hips giving aborted little jerks and thrusts as he tried not to fuck into Sam’s mouth. Every time he swallowed around him, groaned against his groin, sucked hard as he drew back--Crowley was worked up closer to the edge, curling his fingers against Sam’s scalp again, doing his damndest to keep himself in control. He whispered curses and promises half together, everything from pleas to exultations, promised Sam his kingdom if he’d just keep going, don’t stop, oh, don’t ever stop, darling--

But he stopped, pressed forward as far as he could go, gagging a little around the cock twitching in his throat; he shifted his head, moved his tongue, used a hand to squeeze Crowley’s balls tight, and drew back with a loud moan that was only overtaken by Crowley’s shout. The devil came hard, yelling something infernal, shuddering at Sam’s teeth scraping down his shaft and over the spilling head. He milked him dry with his hand, held the tip on his tongue so his semen made a hot pool in the condom set millimeters from his lips and Crowley could just picture it running down his throat instead.

A few more long strips, a couple more drops dragged from him and several moans, and finally Sam leaned back, a little dazed and very, very smug. Crowley chortled at his smirk, leaning back hard against a dust-covered table, and made quick work of removing the condom and tucking himself back in. “Look at you, Moose,” he murmured, but he sounded far less satisfied than he sounded mischievous, so Sam’s smile faded into inquiry.

“Come here,” the devil snickered, gesturing towards the table. “It’s sturdy enough even for the likes of a giant.” 

Blinking, he shifted off his knees--and boy, were those going to bruise--and, after a moment of consideration, sat on the table. Was he not done? It was rare that one orgasm didn’t satisfy Crowley, but, well, there was a first time for everything. He turned his head to ask only to suck in a surprised breath at the hand that undid his belt and jeans with altogether too much practice.

“Wh--Crowley, what are you--”

“Hush now, pet,” murmured the demon, brushing his beard against Sam’s chin in the way he knew he so adored, a cool hand sliding into his jeans and the boxer briefs, sliding right by his plastic packer to press instead into wetness between his lips and pinch the plump clit standing between his legs. “Look at you, and you just weren’t going to tell me how hot and bothered all that got you, were you?”

That answer was a resounding  _ no. _ Sam gasped, wriggling, and found a comfortable space against Crowley’s shoulder with his arm tucked supportively around Sam’s back. “That’s,” he panted out a gasp at a stroke of Crowley’s fingers, “that’s not usually how it g--how it goes.” A shudder ripped its way through him, toes curling in his boots. He was so fucking sensitive, he felt like he was going to explode.

“Well, I suppose I’ve been slacking a little in turnabout,” came the hummed reply. His fingers flattened and dragged across the head of his clit, earning a jolt of Sam’s legs and a strangled moan. He buried his face into Crowley’s neck and grabbed the shreds of his jacket for something to sink his fingers into. When he got back he’d have to change his underwear and hope Dean didn’t notice. “I’ll have to make it up to you, Samuel. They say a good beard is magic between the legs, you know.”

Another shiver, this time yanking his ability to speak right out of his chest. He managed instead to smack the impish smirk right off of Crowley’s lips. “Not a fan of the idea? Not tonight? Fine, fine.” The acquiescence was punctuated by a harder push, fingers swirling circles on his clit. “Not tonight, anyway.”

A scrape of a fingernail was all it took. He tumbled off the edge with a strangled whine, shivering, hips quaking against the hand that continued to pet him through his orgasm and almost pushed him into another. “There, there, kitten,” the devil murmured, “there, there, I have you. Breathe now, sweet.”

He sucked in a deep breath, riding the wave of overstimulation into endorphins. He knew that was what it was, all the medical terms, but his limbs were still heavy and he was still enjoying the scent of aftershave, eyes closed, tears unshed. Crowley quietly pushed his packer back into place and zipped him back up, for once not making a show of licking his fingers clean. 

It took a long minute for his breathing to go back to normal and the pleasant fuzz of afterglow to fade into something manageable, and with a long, leveling sigh he pushed out of Crowley’s arms and pushed himself to his feet. Dean would be calling anytime now for an update. 

Smirking, Crowley crooked a hand in a goodbye. “See you later, Moose. I’m looking forward to it.”

“Bet you are,” he snipped. And, after a second, added, “I’ll, uh, see you later.”


End file.
